Abstract:
:Electrophilic halogenating agents, including hypohalous acids and haloamines, oxidize free methionine and the N-terminal methionines of peptides and proteins (e.g., Met-1 of anti-inflammatory peptide 1 and ubiquitin) to produce dehydromethionine (a five-membered isothiazolidinium heterocycle). Amide derivatives of methionine are oxidized to the corresponding sulfoxide derivatives under the same reaction conditions (e.g., Met-3 of anti-inflammatory peptide 1). Other biological oxidants, including hydrogen peroxide and peroxynitrite, also produce only the corresponding sulfoxides. Hypothiocyanite does not react with methionine residues. We suggest that dehydromethionine may be a useful biomarker for the myeloperoxidase-induced oxidative stress associated with many inflammatory diseases.
journal_name
Biochemistryjournal_title
Biochemistryauthors
Beal JL,Foster SB,Ashby MTdoi
10.1021/bi901343dsubject
Has Abstractpub_date
2009-11-24 00:00:00pages
11142-8issue
46eissn
0006-2960issn
1520-4995journal_volume
48pub_type
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